Modular synthesis of bis(monoacylglycero)phosphate for convenient access to analogues bearing hydrocarbon and perdeuterated acyl chains of varying length

Bis(monoacylglycero)phosphate is an important phospholipid that controls the structure of late endosomes as well as biological activities that occur there. The study of this lipid is complicated by the fact that acyl migrations are known to generate different regioisomers. Herein, we describe a modular synthesis of 3,3'-BMP derivatives that allows for the incorporation of a range of different acyl chains at a late stage. This approach was exploited to produce eight BMP analogues bearing normal saturated and perdeuterated acyl chains of varying length. (C) 2009 Elsevier Ltd. All rights reserved.